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Bioassay-Guided Isolation of a Low Molecular Weight PHB from Burkholderia sp. with Phytotoxic Activity

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Abstract

This work reports on the bioassay-guided isolation and identification of the macrocyclic pentolide 1, a cyclic polyhydroxybutyrate (PHB) with low molecular weight. This metabolite is produced by Burkholderia sp. and it exhibited phytotoxic activity in a Lemna minor bioassay. Its structure was determined by 1H and 13C NMR, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, IR, and electrospray ionization tandem mass spectrometry analyses. The period for maximum production of the pentolide was optimized and determined on the basis of multiple reaction monitoring experiments at 15 days. The potential of Burkholderia sp. as a producer of higher biopolymers of PHB was also investigated. The methodology employed here accelerated the isolation and characterization of a phytotoxic metabolite whose structure can serve as a model for the synthesis of new classes of herbicides.

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References

  1. Godfray, H. C. J., Beddington, J. R., Crute, I. R., Haddad, L., Lawrence, D., Muir, J. F., Pretty, J., Robinson, S., Thomas, S. M., & Toulmin, C. (2010). Science, 327, 812–818.

    Article  CAS  Google Scholar 

  2. Dayan, F. E., Cantrell, C. L., & Duke, S. O. (2009). Bioorganic & Medicinal Chemistry Letters, 17, 4022–4034.

    Article  CAS  Google Scholar 

  3. Dayan, F. E., Owens, D. K., & Duke, S. O. (2012). Pest Management Science, 68, 519–528.

    Article  CAS  Google Scholar 

  4. Saxena, S., & Pandey, A. K. (2005). Applied Microbiology and Biotechnology, 55, 395–403.

    Article  Google Scholar 

  5. Demain, A. L. (1999). Applied Microbiology and Biotechnology, 52, 455–463.

    Article  CAS  Google Scholar 

  6. Duke, S. O., Dayan, F. E., Romagni, J. G., & Rimando, A. M. (2000). Weed Research, 40, 99–111.

    Article  CAS  Google Scholar 

  7. Hynes, R. K., & Boyetchco, S. M. (2006). Soil Biology and Biochemistry, 38, 845–849.

    Article  CAS  Google Scholar 

  8. Piel, J. (2004). Natural Products Reports, 21, 122–124.

    Article  Google Scholar 

  9. Partida-Martinez, L. P., Looß, C. F., Ishida, K., Ishida, M., Roth, M., Buder, K., & Hertweck, C. (2007). Applied and Environmental Microbiology, 73, 793–797.

    Article  CAS  Google Scholar 

  10. Sarma, B. K., & Singh, U. P. (2003). World Journal of Microbiology and Biotechnology, 19, 123–127.

    Article  CAS  Google Scholar 

  11. Xing, J., Xie, C., & Lou, H. J. (2007). Journal of Pharmaceutical and Biomedical Analysis, 44, 368–378.

    Article  CAS  Google Scholar 

  12. Suriyamongkol, P., Weselake, R., Narine, S., Moloney, M., & Sha, S. (2007). Biotechnology Advances, 25, 148–175.

    Article  CAS  Google Scholar 

  13. Seebach, D., Brändli, U., & Schnurrenberger, P. (1988). Helvetica Chimica Acta, 71, 155–167.

    Article  CAS  Google Scholar 

  14. Sasser, M. (1990). UFSCC News, 20, 16–20.

    Google Scholar 

  15. Siciliano, S. D., & Germida, J. J. (1999). FEMS Microbiology Ecology, 29, 263–272.

    Article  CAS  Google Scholar 

  16. Misko, A. M., & Germida, J. J. (2002). FEMS Microbiology Ecology, 42, 399–407.

    Article  CAS  Google Scholar 

  17. Stacjebrandt, E., & Goebel, B. M. (1994). International Journal of Systematic Bacteriology, 44, 846–849.

    Article  Google Scholar 

  18. Standard Guide for conducting toxicity tests with Lemna Gibba. (1993). Annual book of ASTM standards (p. 1232). Philadelphia: American Society for Testing and Materials.

    Google Scholar 

  19. Hoffmann, E. (1996). Journal of Mass Spectrometry, 31, 129–137.

    Article  Google Scholar 

  20. Bourque, D., Pomerleau, Y., & Groleau, D. (1995). Applied Microbiology and Biotechnology, 44, 367–376.

    Article  CAS  Google Scholar 

  21. Chien, C., Chen, C., Choi, M., Kung, S., & Wei, Y. (2007). Journal of Biotechnology, 132, 259–263.

    Article  CAS  Google Scholar 

  22. Wang, J., & Yu, H. (2007). Applied Microbiology and Biotechnology, 75, 871–878.

    Article  CAS  Google Scholar 

  23. Andrade, R. M. F., Valentin, H. E., Berger, P. A., Tran, M., Asrar, J., Gruys, K. J., & Steinbüchel, A. (2000). Applied Microbiology and Biotechnology, 53, 453–460.

    Article  Google Scholar 

  24. Perrotta, J., Stipanovic, A., Nomura, C., & Nakas, J. (2012). Journal of Industrial Microbiology & Biotechnology, 39, 459–469.

    Article  Google Scholar 

  25. Anderson, A. J., & Dawes, E. A. (1990). Microbiological Reviews, 54, 450–472.

    CAS  Google Scholar 

  26. Hamasaki, T., Fuhii, Y., Fukuda, A., Ichimoto, I., & Nakagima, H. (1995). Phytochemistry, 40, 1443–1446.

    Article  Google Scholar 

  27. Lin, W. O., & Neto, J. T. X. B. (1998). Química Nova, 21, 630–635.

    CAS  Google Scholar 

  28. Seebach, D., & Bürger, H. M. (1993). Helvetica Chimica Acta, 76, 94–97.

    Article  Google Scholar 

  29. Seebach, D., Brändli, U., Hans-Martin, M., Dobler, M., Egli, M., Przybylski, M., & Schneider, K. (1989). Helvetica Chimica Acta, 72, 1704–1717.

    Article  CAS  Google Scholar 

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Correspondence to Luiz A. B. Moraes.

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Petta, T., Raichardt, L., Melo, I.S. et al. Bioassay-Guided Isolation of a Low Molecular Weight PHB from Burkholderia sp. with Phytotoxic Activity. Appl Biochem Biotechnol 170, 1689–1701 (2013). https://doi.org/10.1007/s12010-013-0292-1

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  • DOI: https://doi.org/10.1007/s12010-013-0292-1

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